612
L. Werner et al. / Tetrahedron Letters 48 (2007) 609–612
´
´
´ˇ
´
L.; Dvorˇakova, H.; Vojtısek, P. Tetrahedron: Asymmetry
73.43, 72.80, 71.35, 69.11 (CH2), 82.19, 80.02, 78.17, 71.35
(CH-20, CH-30, CH-40, CH-50), 81.55 (CH-4), 75.38 (CH-
10), 61.39 (CH-5), 45.54 (CH2-1), 42.55 (CH-3), 32.68
(CH2-2), 26.54 (CH2-100). ES MS: 848.3 (M+1).
ˇ´
´
2004, 15, 1033–1041; (c) Vıch, O.; Kniezˇo, L.; Dvorakova,
H.; Raich, I.; Valenta, S. Collect. Czech. Chem. Commun.
2005, 70, 2086–2100.
ˇ
17. (a) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31,
6777–6780; (b) Matos, C. R. R.; Lopes, R. S. C.; Lopes, C.
C. Synthesis 1999, 571–573.
18. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61,
6987–6993.
Selected data of compound 15: 1H NMR (500.13 MHz,
CDCl3) d 7.12–7.44 (m, 30H, H arom.), 4.32–4.99 (m,
12H, CH2Ph), 4.10 (ddd, 1H, H-10, J(10,20) =
J(10,100A) = 2.6 Hz, J(10,100B) = 12.4 Hz), 3.53–3.86 (m,
8H, H20, H30, H40, H50, CH2-60, CH2-6), 3.04–3.16
(m,2H, overlap H-1, H-4), 2.74 (m, 1H, H-5), 2.60
(ddd, 1H, H-1ax, J(1ax,1eq) = J(1ax,2ax) = 12.3 Hz,
19. Selected data of compound 14: 1H NMR (500.13 MHz,
CDCl3) d 7.11–7.42 (m, 30H, H arom.), 4.42–4.99 (m,
12H, CH2Ph), 4.22 (ddd, 1H, H-10, J(10,100A) = 12.7 Hz,
J(10,20) = 5.8 Hz, J(10,100B) = 2.6 Hz), 3.56–3.80 (m, 8H,
H20, H30, H40, H50, CH2-60, CH2-6), 3.03 (dd, 1H, H-4,
J(4,3) = J(4,5) = 9.7 Hz), 2.95 (ddd, 1H, H-1eq,
J(1eq,1ax) = 12.2 Hz, J(1eq,2ax) = 4.0 Hz, J(1eq,2eq) ꢁ
1 Hz), 2.78 (m, 1H, H-5), 2.57 (ddd, 1H, H-1ax,
J(1ax,1eq) = 12.2 Hz, J(1ax,2ax) = 10.3 Hz, J(1ax,2eq) =
2.1 Hz), 2.33 (ddd, 1H, H-100B, J(100B,100A) = 14.6 Hz,
J(100B,10) = 2.6 Hz, J(100B,3) = 3.4 Hz), 2.14 (dddd,
1H, H-2eq, J(2eq,2ax) = 10.8 Hz, J(2eq,1ax) = 2.1,
J(2eq,3) = J(2eq,1eq) ꢁ 1 Hz), 1.74 (m, 1H, H-3), 1.48
(ddd, 1H, H-100A, J(100A,100B) = 14.6 Hz, J(100A,10) =
12.7 Hz, J(100A,3) = 8.3 Hz), 1.24 (dddd, 1H, H-2ax,
J(1ax,2eq) = 1.8 Hz),
2.31
(ddd,
1H,
H-100B,
J(100B,100A) = 13.5 Hz, J(100B,10) = 12.4 Hz, J(100B,3) ꢁ
0 Hz), 1.90 (dddd, 1H, H-2eq, J(2eq,2ax) = 12.2 Hz,
J(2eq,1ax) = 1.8 Hz, J(2eq,3) = J(2eq,1eq) ꢁ 1 Hz), 1.69
(m, 1H, H-3), 1.30 (ddd, 1H, H-100A, J(100A,100B) =
13.5 Hz, J(100A,3) = 12.0 Hz, J(100A,10) = 2.6 Hz), 1.20
(dddd, 1H, H-2ax, J(2ax,2eq) = 12.2 Hz, J(2ax,1ax) =
1
J(2ax,3) = 12.5 Hz, J(2ax,1eq) = 3.2 Hz). H NMR of H-
4 and H-1eq (500.13 MHz, CD2Cl2) d 3.13 (dd, 1H, H-4,
J(4,3) = J(4,5) = 9.8 Hz), 3.09 (m, 1H, H-1eq). 13C NMR
(125.77 MHz, CDCl3) d 138.80, 138.68, 138.29, 138.28,
138.01, 137.91, 137.88 (C arom.), 128.57, 128.44, 128.34,
128.22, 128.17, 128.07, 127.99, 127.95, 127.89, 127.80,
127.78, 127.58, 127.55, 127.40 (CH arom.), 75.44, 74.97,
74.63, 73.51, 73.23, 73.18, 68.90 (CH2), 82.54, 80.14, 78.13,
70.50 (CH-20, CH-30, CH-40, CH-50), 80.14 (CH-4), 70.13
(CH-10), 61.60 (CH-5), 45.23 (CH2-1), 37.78 (CH-3), 30.34
(CH2-2), 26.46 (CH2-100). ES MS: 848.3 (M+1).
J(2ax,2eq) = 10.8 Hz,
J(2ax,1ax) = J(2ax,3) = 12.5 Hz,
J(2ax,1eq) = 4.0 Hz). 13C NMR (125.77 MHz, CDCl3) d
138.71, 138.19, 138.11, 138.01 (C arom.), 128.42, 128.36,
128.29, 127.91, 127.85, 127.79, 127.73, 127.69, 127.62,
127.60, 127.54 (CH arom.), 75.31, 75.01, 73.86, 73.47,